US2018105840A1PendingUtilityA1

Process for industrial production of chiral-1,1-difluoro-2-propanol

Assignee: PUBLIC UNIV CORPORATION TOYAMA PREFECTURAL UNIVPriority: Mar 3, 2015Filed: Mar 2, 2016Published: Apr 19, 2018
Est. expiryMar 3, 2035(~8.6 yrs left)· nominal 20-yr term from priority
C12N 1/16C07C 19/08C07C 31/10C12P 7/04C12P 41/002C07C 31/38
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Claims

Abstract

The present invention provides a process for industrial production of chiral-1,1-difluoro-2-propanol. More specifically, a microorganism having the activity to cause asymmetric reduction of 1,1-difluoroacetone or an enzyme having the same activity is allowed to act on 1,1-difluoroacetone, whereby chiral-1,1-difluoro-2-propanol can be produced with high optical purity and in good yield. The process for production of the present invention is easy for industrial implementation.

Claims

exact text as granted — not AI-modified
1 . A process for production of chiral-1,1-difluoro-2-propanol represented by formula [2], wherein a microorganism having the activity to cause asymmetric reduction of 1,1-difluoroacetone or an enzyme having the same activity is allowed to act on 1,1-difluoroacetone represented by formula [1]: 
       
         
           
           
               
               
           
         
       
       [wherein the asterisk (*) represents an asymmetric atom]. 
     
     
         2 . The process for production according to  claim 1 , wherein the microorganism is at least one selected from the group consisting of  Candida guilliermondii, Candida parapsilosis, Candida vini, Candida viswanathii, Cryptococcus laurentii, Cryptococcus curvatus, Debaryomyces maramus, Kluyveromyces marxianus, Ogataea polymorpha, Pichia anomala, Pichia farinosa, Pichia haplophila, Pichia minuta, Rhodotorula muculaginosa, Saccharomyces rouxii, Torulaspora delbrueckii, Wickerhamomyces subpelliculosa,  and  Zygosaccharomyces rouxii.    
     
     
         3 . The process for production according to  claim 2 , wherein the microorganism is selected from the microorganisms having Accession Nos. indicated in the table below. 
       
         
           
                 
                 
                 
               
                   TABLE 1 
                 
                     
                 
                     
                   Accession 
                     
                 
                   Microorganism 
                   No. 
                   Depository institution 
                 
                     
                 
                   
                     Candida guilliermondii 
                   
                   NBRC10279 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Candida parapsilosis 
                   
                   NBRC0708 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Candida vini 
                   
                   NBRC1247 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Candida viswanathii 
                   
                   NBRC10321 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Cryptococcus laurentii 
                   
                   NBRC0609 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Cryptococcus curvatus 
                   
                   NBRC1159 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Debaryomyces maramus 
                   
                   NBRC0668 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Kluyveromyces marxianus 
                   
                   NBRC10005 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Ogataea polymorpha 
                   
                   NBRC0799 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Pichia anomala 
                   
                   NBRC0118 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Pichia farinosa 
                   
                   NBRC0462 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Pichia haplophila 
                   
                   NBRC0947 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Pichia minuta 
                   
                   NBRC0975 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Rhodotorula muculaginosa 
                   
                   NBRC0001 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Saccharomyces rouxii 
                   
                   NBRC0493 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Torulaspora delbrueckii 
                   
                   NBRC0381 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Wickerhamomyces 
                   
                   NBRC0198 
                   National Institute of 
                 
                   
                     subpelliculosa 
                   
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                   
                     Zygosaccharomyces rouxii 
                   
                   NBRC10671 
                   National Institute of 
                 
                     
                     
                   Technology and Evaluation, 
                 
                     
                     
                   Independent Administrative 
                 
                     
                     
                   Agency 
                 
                     
                 
             
                
                
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         4 . The process for production according to any one of  claims 1  to  3 , wherein the microorganism is allowed to act as whole microbial cells or as a cell extract thereof. 
     
     
         5 . The process for production according to  claim 1 , wherein the enzyme is a purified enzyme derived from  Ogataea polymorpha, Ogataea parapolymorpha, Pichia anomala,  or  Pichia minuta.    
     
     
         6 . The process for production according to  claim 5 , wherein the  Ogataea polymorpha  is  Ogataea polymorpha  strain NBRC0799. 
     
     
         7 . The process for production according to  claim 1 , wherein the temperature at which the microorganism or enzyme is allowed to act is 5° C. to 60° C. 
     
     
         8 . The process for production according to  claim 1 , wherein the pH at which the microorganism or enzyme is allowed to act is in the range of 4.0 to 8.0. 
     
     
         9 . The process for production according to  claim 1 , which further comprises a step where the mixture containing 1,1-difluoro-2-propanol and impurities obtained after the microorganism or enzyme is allowed to act is distilled to separate the impurities from the mixture and thereby purify 1,1-difluoro-2-propanol.

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